Reactive hot melt adhesive composition and use thereof

Patent metadata

Field	Value
Publication number	US-12378453-B2
Application number	US-202217813680-A
Country	US
Kind code	B2
Filing date	Jul 20, 2022
Priority date	Feb 13, 2020
Publication date	Aug 5, 2025
Grant date	Aug 5, 2025

Abstract

The present invention relates to a reactive hot melt adhesive composition and the use thereof. In particular, the present invention provides an adhesive having excellent washing resistance, especially having excellent resistance to antibacterial laundry cleansers. In addition, the adhesive has very short open time and good softness upon curing.

First claim

What is claimed is:

1. A reactive hot melt adhesive composition comprising at least one NCO-terminated polyurethane prepolymer, wherein the NCO-terminated polyurethane prepolymer comprises the reaction product of a mixture comprising:
at least one polyisocyanate;
at least one polytetrahydrofuran; and
at least one polyol different from the at least one polytetrahydrofuran and not including a polyester polyol, wherein:
a molar ratio of the NCO group of the at least one polyisocyanate to the total OH groups of the at least one polytetrahydrofuran and the at least one polyol is from about 1.5 to about 2.5, and
the at least one polytetrahydrofuran is in an amount of from about 20% to about 60% by weight, based on the total weight of the NCO-terminated polyurethane prepolymer.

2. The reactive hot melt adhesive composition of claim 1 , wherein the amount of the NCO group is from about 1% to about 5% by weight, based on the total weight of the NCO-terminated polyurethane prepolymer.

3. The reactive hot melt adhesive composition of claim 1 , wherein the at least one polyisocyanate is a diisocyanate selected from the group consisting of 2,2′-methylene diphenyl diisocyanate, 4,4′-methylene diphenyl diisocyanate, 2,4′-methylene diphenyl diisocyanate, 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, 1,6-hexamethylene diisocyanate, isophorone diisocyanate, and any combination thereof.

4. The reactive hot melt adhesive composition of claim 1 , wherein the at least one polytetrahydrofuran has a number average molecular weight (Mn) of from about 1,000 g/mol to about 5,000 g/mol.

5. The reactive hot melt adhesive composition of claim 4 , wherein the at least one polytetrahydrofuran has a number average molecular weight (Mn) of from about 1,000 g/mol to about 3,500 g/mol.

6. The reactive hot melt adhesive composition of claim 1 , wherein the at least one polyol is amorphous and has a glass transition temperature (Tg) of from about −40° C. to about 40° C.

7. The reactive hot melt adhesive composition of claim 1 , wherein:
the at least one polyisocyanate is in an amount of from about 10% to about 40%, based on the total weight of the NCO-terminated polyurethane prepolymer,
the at least one polytetrahydrofuran is in an amount of from about 20% to about 60%, based on the total weight of the NCO-terminated polyurethane prepolymer, and
the at least one polyol is in an amount of from about 20% to about 60%, based on the total weight of the NCO-terminated polyurethane prepolymer.

8. The reactive hot melt adhesive composition of claim 1 , wherein the melting temperature of the reactive hot melt adhesive composition is from about 100 to about 140° C.

9. A cured product comprising the reactive hot melt adhesive composition of claim 1 .

10. The cured product of claim 9 , wherein the cured product exhibits a bonding strength retention after washing of more than about 75%, wherein the bonding strength retention is calculated by dividing the bonding strength of the cured product after washing by the bonding strength of the cured product before washing.

11. An article comprising two textile substrates bonded by the cured product of claim 9 .

12. A garment or undergarment comprising two textile substrates bonded by the cured product of claim 9 .

13. A reactive hot melt adhesive composition comprising at least one NCO-terminated polyurethane prepolymer, wherein the NCO-terminated polyurethane prepolymer comprises the reaction product of a mixture comprising:
4′4-methylene diphenyl diisocyanate in an amount of from 15% to about 35% by weight, based on the total weight of the NCO-terminated polyurethane prepolymer;
polytetrahydrofuran in an amount of from about 20% to about 60% by weight, based on the total weight of the NCO-terminated polyurethane prepolymer; and
at least one polyol in an amount of from about 1.2% to about 4% by weight, based on the total weight of the NCO-terminated polyurethane prepolymer, the at least one polyol being selected from polyether polyols other than polytetrahydrofuran, polyester polyols, and any combination thereof, wherein:
a molar ratio of the NCO group of the 4′4-methylene diphenyl diisocyanate to the total OH groups of the polytetrahydrofuran and the at least one polyol is from about 1.5 to about 2.5, and
the amount of the NCO group is from about 1.2% to about 4% by weight, based on the total weight of the NCO-terminated polyurethane prepolymer.

14. The reactive hot melt adhesive composition of claim 13 , wherein the polytetrahydrofuran has a number average molecular weight (Mn) of from about 1,000 g/mol to about 5,000 g/mol.

15. The reactive hot melt adhesive composition of claim 14 , wherein the polytetrahydrofuran has a number average molecular weight (Mn) of from about 1,000 g/mol to about 3,500 g/mol.

16. A cured product comprising the reactive hot melt adhesive composition of claim 13 .

17. The cured product of claim 16 , wherein the cured product exhibits a bonding strength retention after washing of more than about 75%, wherein the bonding strength retention is calculated by dividing the bonding strength of the cured product after washing by the bonding strength of the cured product before washing.

18. An article comprising two textile substrates bonded by the cured product of claim 16 .

19. A garment or undergarment comprising two textile substrates bonded by the cured product of claim 16 .

Assignees

• Henkel Ag & Co Kgaa

Inventors

• Zhu Hongye
• Che Aifu

Classifications

• C09J2475/00

  Presence of polyurethane · CPC title

• C09J2400/266

  in the pretreated surface to be joined · CPC title

• C09J5/06

  involving heating of the applied adhesive · CPC title

• C08G18/7671 Primary

  containing only one alkylene bisphenyl group · CPC title

• C08G18/4202

  Two or more polyesters of different physical or chemical nature (C08G18/44 takes precedence) · CPC title